Methyl nomilinate from citrus can modulate cell cycle regulators to induce cytotoxicity in human colon cancer (SW480) cells in vitro

Toxicology in Vitro

Volumn 26, Issue 7, 2012, Pages 1216-1223

  Kim, Jinhee ^a   Jayaprakasha, Guddadarangavvanahally K ^a   Vikram, Amit ^a   Patil, Bhimanagouda S ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

Apoptosis; Cell cycle arrest; Citrus; Methyl nomilinate; SW480

Indexed keywords

CAMPTOTHECIN; CASPASE 3; CITRUS FRUIT EXTRACT; CITRUS LEMON EXTRACT; CYCLIN D3; CYCLIN DEPENDENT KINASE 4; CYCLIN DEPENDENT KINASE 6; ISOLIMONEXIC ACID; ISOOBACUNOIC ACID; LIMONEXIC ACID; LIMONOID; METHYL NOMILINATE; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CANCER CELL; CANCER CELL CULTURE; CANCER INHIBITION; CELL ACTIVITY; CELL CYCLE G0 PHASE; CELL CYCLE REGULATION; CELL METABOLISM; CELL PROLIFERATION; COLON ADENOCARCINOMA; CONTROLLED STUDY; DRUG DETERMINATION; DRUG EFFICACY; DRUG PURIFICATION; DRUG STRUCTURE; ENZYME REPRESSION; G1 PHASE CELL CYCLE CHECKPOINT; HUMAN; HUMAN CELL; IN VITRO STUDY; LEMON; PROTEIN EXPRESSION; TREATMENT RESPONSE;

ADENOCARCINOMA; ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL CYCLE; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; CITRUS; COLONIC NEOPLASMS; CYCLIN D3; CYCLIN-DEPENDENT KINASE 4; CYCLIN-DEPENDENT KINASE 6; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; HUMANS; LIMONINS; PLANT EXTRACTS;

CITRUS;

EID: 84866022495     PISSN: 08872333     EISSN: 18793177     Source Type: Journal    
DOI: 10.1016/j.tiv.2012.06.005     Document Type: Article

References (51)

1. Abdelrahim M., Smith R., Burghardt R., Safe S. Role of Sp proteins in regulation of vascular endotherial growth factor expression and proliferation of pancreatic cancer cells. Cancer Res. 2004, 64:6470-6479.
2. Bennett R.D., Hasegawa S., Zareb H. Glucosides of acidic limonoids in citrus. Phytochemistry 1989, 28:2777-2781.
3. Bismuth H., Adam R., Levi F., Farabos C., Waechter F., Castaing D., Majno P., Engerran L. Resection of nonresectable liver metastases from colorectal cancer after neoadjuvant chemotherapy. Ann. Surg. 1996, 224:509-522.
4. Buck S., Bradford J., Gee K., Agnew B., Clarke S., Salic A. Detection of S-phase cell cycle progression using 5-ethynyl-2'-deoxyuridine incorporation with click chemistry, an alternative to using 5-bromo-2'-deoxyuridine antibodies. Biotechniques 2008, 44:927-929.
5. Chidambara Murthy K.N., Jayaprakasha, G.K., Patil, B.S. Obacunone and obacunone glucoside inhibit human colon cancer (SW480) cells by the induction of apoptosis. Food Chem. Toxicol. 2011, 49:1616-1625.
6. Chiruvella K., Mohammed A., Dampuri G., Ghanta R., Raghavan S. Phytochemical and antimicrobial studies of methyl angolensate and luteolin-7-O-glucoside isolated from callus cultures of Soymida febrifuga. Int. J. Biomed. Sci. 2007, 3:269-278.
7. Germain M., Affar E.B., D'Amours D., Dixit V.M., Salvesen G.S., Poirier G.G. Cleavage of automodified poly(ADP-ribose) polymerase during apoptosis. J. Biol. Chem. 1999, 274:28379-28384.
8. González-Molina E., Domínguez-Perles R., Moreno D., García-Viguera C. Natural bioactive compounds of citrus limon for food and health. J. Pharm. Biomed. Anal. 2009, 51:327-345.
9. Guthrie N., Morley K., Hasegawa S., Manners G.D., Vandenberg T. Inhibition of human breast cancer cells by citrus limonoids. Citrus Limonoids 2000, vol. 758:164-174. Springer, Washington, DC.
10. Hasegawa, S., Kim, K., 1975. Biochemistry of limonoids. A new limonoid-debittering enzyme. In: Citrus Research Conference. Agricultural Research Service, Fruit and Vegetable Chemistry Laboratory, United States.
11. Herceg Z., Wang Z. Functions of poly (ADP-ribose) polymerase (PARP) in DNA repair, genomic integrity and cell death. Mutat. Res. Fundam. Mol. Mech. Mutag. 2001, 477:97-110.
12. Jayaprakasha G.K., Jadegoud Y., Nagana Gowda G.A., Patil B.S. Bioactive compounds from sour orange inhibit colon cancer cell proliferation and induce cell cycle arrest. J. Agric. Food Chem. 2010, 58:180-186.
13. Jayaprakasha G.K., Mandadi K.K., Poulose S.M., Jadegoud Y., Nagana G., Patil B.S. Novel triterpenoid from Citrus aurantium L. possesses chemopreventive properties against human colon cancer cells. Bioorg. Med. Chem. 2008, 16:5939-5951.
14. Jayaprakasha G.K., Patil B.S. In vitro evaluation of the antioxidant activities in fruit extracts from citron and blood orange. Food Chem. 2007, 101:410-418.
15. Kelly C., Jewell C., O'Brien N.M. The effect of dietary supplementation with the citrus limonoids, limonin and nomilin on xenobiotic-metabolizing enzymes in the liver and small intestine of the rat. Nutr. Res. 2003, 23:681-690.
16. Kim J., Jayaprakasha G.K., Uckoo R.M., Patil B.S. Evaluation of chemopreventive and cytotoxic effect of lemon seed extracts on human breast cancer (MCF-7) cells. Food Chem. Toxicol. 2012, 50:423-430.
17. Klabunde C., Lanier D., Breslau E., Zapka J., Fletcher R., Ransohoff D., Winawer S. Improving colorectal cancer screening in primary care practice: innovative strategies and future directions. J. Gen. Intern. Med. 2007, 22:1195-1205.
18. Kurowska E.M., Banh C., Hasegawa S., Manners G.D. Regulation of apo production in HepG2 cells by citrus limonoids. Citrus limonoids 2000, vol. 758:175-184. American Chemical Society, Inc., Washington, DC.
19. Kushi L., Byers T., Doyle C., Bandera E., McCullough M., Gansler T., Andrews K., Thun M. American Cancer Society Guidelines on Nutrition and Physical Activity for cancer prevention: reducing the risk of cancer with healthy food choices and physical activity. CA Cancer J. Clin. 2006, 56:254-281.
20. Lam L.K.T., Hasegawa S. Inhibition of benzo [a] pyrene-induced forestomach neoplasia in mice by citrus limonoids. Nutr. Cancer 1989, 12:43-47.
21. Lam L.K.T., Zhang J., Hasegawa S. Citrus limonoid reduction of chemically induced tumorigenesis. Food Technol. 1994, 48:104-108.
22. Liu L.F., Desai S.D., Li T.K., Mao Y., Sun M., Sim S.P. Mechanism of action of camptothecin. Ann. N. Y. Acad. Sci. 2000, 922:1-10.
23. Longley D., Harkin D., Johnston P. 5-fluorouracil: mechanisms of action and clinical strategies. Nat. Rev. Cancer 2003, 3:330-338.
24. Maier V.P., Grant E.R. Specific thin-layer chromatography assay of limonin, a citrus bitter principle. J. Agric. Food Chem. 1970, 18:250-252.
25. Malumbres M., Barbacid M. Cell cycle, CDKs and cancer: a changing paradigm. Nat. Rev. Cancer 2009, 9:153-166.
26. Manners G., Jacob R., Breksa A., Schoch T., Hasegawa S. Bioavailability of citrus limonoids in humans. J. Agric. Food Chem. 2003, 51:4156-4161.
27. Massagué J. G1 cell-cycle control and cancer. Nature 2004, 432:298-306.
28. Patil B.S., Brodbelt J.S., Miller E.G., Turner N.D. Potential health benefits of citrus: an overview. Potential Health Benefits of Citrus 2006, 1-16. American Chemical Society, Inc., Washington, DC. B. S Patil, N.D. Turner, E.G. Miller, J. S Brodbelt (Eds.).
29. Patil J., Kim J., Jayaprakasha G. Berberine induces apoptosis in breast cancer cells (MCF-7) through mitochondrial-dependent pathway. Eur. J. Pharmacol. 2010, 645:70-78.
30. Patil J.R., Jayaprakasha G.K., Murthy K.N.C., Chetti M.B., Patil B.S. Characterization of Citrus aurantifolia bioactive compounds and their inhibition of human pancreatic cancer cells through apoptosis. Microchem. J. 2010, 94:108-117.
31. Patil J.R., Murthy K.N.C., Jayaprakasha G.K., Chetti M.B., Patil B.S. Bioactive compounds from Mexican lime (Citrus aurantifolia) juice induce apoptosis in human pancreatic cells. J. Agric. Food Chem. 2009, 57:10933-10942.
32. Pellegata N.S., Sessa F., Renault B., Bonato M., Leone E., Solcia E., Ranzani G.N. K-ras and p53 gene mutations in pancreatic cancer: ductal and nonductal tumors progress through differnet genetic lesions. Cancer Res. 1994, 54:1556-1560.
33. Perez J.L., Jayaprakasha G.K., Valdivia V., Munoz D., Dandekar D.V., Ahmad H., Patil B.S. Limonin methoxylation influences the induction of glutathione S-transferase and quinone reductase. J. Agric. Food Chem. 2009, 57:5279-5286.
34. Pettit G.R., Barton D.H.R., Herald C.L., Polonsky J., Schmidt J.M., Connolly J.D. Evaluation of limonoids against the murine P388 lymphocytic leukemia cell line. J. Nat. Prod. 1983, 46:379-390.
35. Pietenpol J., Stewart Z. Cell cycle checkpoint signaling: cell cycle arrest versus apoptosis. Toxicology 2002, 181:475-481.
36. Poulose S.M., Harris E.D., Patil B.S. Antiproliferative effects of citrus limonoids against human neuroblastoma and colonic adenocarcinoma cells. Nutr. Cancer 2006, 56:103-112.
37. Riccardi C., Nicoletti I. Analysis of apoptosis by propidium iodide staining and flow cytometry. Nat. Protoc. 2006, 1:1458-1461.
38. Rodrigues N.R., Rowan A., Smith M.E., Kerr I.B., Bodmer W.F., Gannon J.V., Lane D.P. p53 mutations in colorectal cancer. Proc. Natl. Acad. Sci. 1990, 87:7555-7559.
39. Roy A., Saraf S. Limonoids: overview of significant bioactive triterpenes distributed in plants kingdom. Biol. Pharm. Bull. 2006, 29:191-201.
40. Silalahi J. Anticancer and health protective properties of citrus fruit components. Asia Pac. J. Clin. Nutr. 2002, 11:79-84.
41. Society A.C. Cancer Facts and Figures 2009, American Cancer Society, Atlanta.
42. Spreen T.H. Projections of world production and consumption of citrus to 2010. Fruit Process. 2003, 13:378-384.
43. Tanaka T., Maeda M., Kohno H., Murakami M., Kagami S., Miyake M., Wada K. Inhibition of azoxymethane-induced colon carcinogenesis in male F344 rats by the citrus limonoids obacunone and limonin. Carcinogenesis 2001, 22:193-198.
44. Tian Q., Miller E.G., Ahmad H., Tang L., Patil B.S. Differential inhibition of human cancer cell proliferation by citrus limonoids. Nutr. Cancer 2001, 40:180-184.
45. Vanamala J., Leonardi T., Patil B.S., Taddeo S.S., Murphy M.E., Pike L.M., Chapkin R.S., Lupton J.R., Turner N.D. Suppression of colon carcinogenesis by bioactive compounds in grapefruit. Carcinogenesis 2006, 27:1257-1265.
46. Vikram, A., 2011. Citrus bioactive compounds: isolation, characterization and modulation of bacterial intercellular communication and virulence. Horticultural Sciences, Ph.D. Dissertation. Texas A&M University, College Station, p. 292.
47. Vikram A., Jayaprakasha G.K., Patil B.S. Simultaneous determination of citrus limonoid aglycones and glucosides by high performance liquid chromatography. Anal. Chim. Acta 2007, 590:180-186.
48. Vikram A., Jesudhasan P.R., Jayaprakasha G., Pillai S.D., Patil B.S. Citrus limonoids interfere with Vibrio harveyi cell-cell signalling and biofilm formation by modulating the response regulator LuxO. Microbiology 2011, 157:99-110.
49. WHO, 2009. Cancers. In Fact Sheet. World Health Organization.
50. Yan N., Shi Y. Mechanisms of apoptosis through structural biology. Annu. Rev. Cell Dev. Biol. 2005, 21:35-56.
51. Yu J., Wang L., Walzem R.L., Miller E.G., Pike L.M., Patil B.S. Antioxidant activity of citrus limonoids, flavonoids, and coumarins. J. Agric. Food Chem. 2005, 53:2009-2014.